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cine Substitution and the Cu Effect in Stille Cross‐Coupling Reactions: Mechanistic Perspectives and Synthetic Utility
Author(s) -
Peng Yu,
Li WeiDong Z.
Publication year - 2010
Publication title -
european journal of organic chemistry
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.825
H-Index - 155
eISSN - 1099-0690
pISSN - 1434-193X
DOI - 10.1002/ejoc.201000557
Subject(s) - stille reaction , transmetalation , chemistry , steric effects , substitution (logic) , catalysis , coupling reaction , coupling (piping) , selectivity , combinatorial chemistry , stereochemistry , organic chemistry , materials science , computer science , metallurgy , programming language
cine Substitution arising from slow transmetallation occasionally occurs in classic Pd‐catalyzed Stille cross‐coupling reactions with sterically hindered vinyltin components. Mechanistic explanations of this “abnormal” cross‐coupling mode and the intriguing co‐catalytic effects of metallic Cu species in restoring the ipso selectivity are summarized. Typical synthetic applications of this unique Cu effect and the advent of Cu‐catalyzed Stille‐type cross‐coupling are also demonstrated.